CA2873793C - Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase - Google Patents

Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase Download PDF

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Publication number
CA2873793C
CA2873793C CA2873793A CA2873793A CA2873793C CA 2873793 C CA2873793 C CA 2873793C CA 2873793 A CA2873793 A CA 2873793A CA 2873793 A CA2873793 A CA 2873793A CA 2873793 C CA2873793 C CA 2873793C
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bcn
group
polypeptide
amino acid
tetrazine
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CA2873793A
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English (en)
French (fr)
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CA2873793A1 (en
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Jason Chin
Kathrin Lang
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United Kingdom Research and Innovation
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United Kingdom Research and Innovation
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Priority claimed from GBGB1208875.3A external-priority patent/GB201208875D0/en
Priority claimed from GBGB1210303.2A external-priority patent/GB201210303D0/en
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Publication of CA2873793A1 publication Critical patent/CA2873793A1/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K1/00General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/006General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/08Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K1/00General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/13Labelling of peptides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K2/00Peptides of undefined number of amino acids; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/93Ligases (6)
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12YENZYMES
    • C12Y601/00Ligases forming carbon-oxygen bonds (6.1)
    • C12Y601/01Ligases forming aminoacyl-tRNA and related compounds (6.1.1)
    • C12Y601/01026Pyrrolysine-tRNAPyl ligase (6.1.1.26)
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14All rings being cycloaliphatic
    • C07C2602/24All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • Biomedical Technology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Urology & Nephrology (AREA)
  • Cell Biology (AREA)
  • Food Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Peptides Or Proteins (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
CA2873793A 2012-05-18 2013-05-15 Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase Active CA2873793C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB1208875.3 2012-05-18
GBGB1208875.3A GB201208875D0 (en) 2012-05-18 2012-05-18 Methods
GB1210303.2 2012-06-08
GBGB1210303.2A GB201210303D0 (en) 2012-06-08 2012-06-08 Polypeptides and methods
PCT/GB2013/051249 WO2013171485A1 (en) 2012-05-18 2013-05-15 Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase.

Publications (2)

Publication Number Publication Date
CA2873793A1 CA2873793A1 (en) 2013-11-21
CA2873793C true CA2873793C (en) 2022-02-22

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CA2873793A Active CA2873793C (en) 2012-05-18 2013-05-15 Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase

Country Status (8)

Country Link
US (3) US20150148525A1 (enExample)
EP (1) EP2852664B1 (enExample)
JP (1) JP6343604B2 (enExample)
CN (2) CN108410827B (enExample)
BR (1) BR112014028588B1 (enExample)
CA (1) CA2873793C (enExample)
IN (1) IN2014DN09922A (enExample)
WO (1) WO2013171485A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2852664B1 (en) 2012-05-18 2017-09-06 Medical Research Council Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase.
CN106010507A (zh) * 2013-12-31 2016-10-12 深圳先进技术研究院 由染料分子标记的四嗪探针及其制备方法和应用
GB2528227A (en) 2014-03-14 2016-01-20 Medical Res Council Cyclopropene amino acids and methods
EP3288925B1 (en) * 2015-04-30 2021-09-01 Oregon State University Reagents and methods for bioorthogonal labeling of biomolecules in living cells
US10906990B2 (en) * 2015-08-19 2021-02-02 Riken Antibody with non-natural amino acid introduced therein
CN105254655B (zh) * 2015-11-20 2017-03-22 江汉大学 一种基于bodipy的荧光氨基酸及其合成方法与应用
CN106565762B (zh) * 2016-11-17 2018-10-23 陕西师范大学 一种原位产生近红外荧光的bodipy类染料及其制备和应用
AR111190A1 (es) 2017-03-22 2019-06-12 Genentech Inc Composiciones en hidrogel de prodrogas entrecruzadas de ácido hialurónico y métodos relacionados
JOP20190245A1 (ar) 2017-04-20 2019-10-15 Novartis Ag أنظمة توصيل إطلاق مستدام تتضمن روابط بلا أثر لنقطة الربط
US11560384B2 (en) 2017-05-04 2023-01-24 University Of Utah Research Foundation Benzonorbornadiene derivatives and reactions thereof
AR111963A1 (es) * 2017-05-26 2019-09-04 Univ California Método y moléculas
AR116566A1 (es) 2018-10-03 2021-05-19 Novartis Ag Administración sostenida de polipéptidos similares a la angiopoyetina 3
GB201817444D0 (en) 2018-10-26 2018-12-12 Res & Innovation Uk Methods and compositions
CN111849929B (zh) * 2019-04-30 2021-05-11 苏州鲲鹏生物技术有限公司 高效引入赖氨酸衍生物的氨酰基—tRNA合成酶
GB201906775D0 (en) 2019-05-14 2019-06-26 Res & Innovation Uk Synthetic genome
IL267744A (en) * 2019-06-30 2019-08-29 Nat Inst Biotechnology Negev Ltd Labelling molecules and methods of use thereof
CN115701451B (zh) * 2021-08-02 2023-08-01 宁波鲲鹏生物科技有限公司 高效引入赖氨酸衍生物的氨酰基-tRNA合成酶及其应用
WO2024223922A1 (en) 2023-04-28 2024-10-31 United Kingdom Research And Innovation ACYL-tRNA SYNTHETASES
GB202307998D0 (en) 2023-05-29 2023-07-12 Res & Innovation Uk Aminoacyl-irna synthetase sets
CN119613545B (zh) * 2024-12-16 2025-09-16 天津大学 非天然氨基酸修饰的抗ccl5纳米抗体

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040029129A1 (en) * 2001-10-25 2004-02-12 Liangsu Wang Identification of essential genes in microorganisms
CN102618605B (zh) 2003-06-18 2015-09-02 斯克利普斯研究院 非天然活性氨基酸遗传密码增加
ATE471385T1 (de) * 2003-07-07 2010-07-15 Scripps Research Inst Zusammensetzungen aus orthogonalen lysyl-trna- und aminoacyl-trna-synthetasepaaren und deren verwendung
BRPI0417801A (pt) 2003-12-18 2007-04-10 Scripps Research Inst incorporação seletiva de 5-hidroxitriptofano em proteìnas de células mamìferas
ES2519444T3 (es) 2004-09-21 2014-11-07 The Scripps Research Institute Incorporación in vivo de alquinil aminoácidos a proteínas en eubacterias
EP1807515A4 (en) 2004-10-27 2008-06-18 Scripps Research Inst Orthogonal translation components for the in vivo incorporation of unnatural amino acids
US8431558B2 (en) * 2004-11-01 2013-04-30 The Regents Of The University Of California Compositions and methods for modification of biomolecules
JP2007037445A (ja) 2005-08-02 2007-02-15 Institute Of Physical & Chemical Research tRNA合成方法、核酸、アミノアシルtRNA合成方法及び非天然型アミノ酸組み込み蛋白質の製造方法
WO2007090198A2 (en) 2006-02-01 2007-08-09 Encode Bio, Inc. Fluorescent assays using orthogonal trna - aminoacyl synthetase pairs
US20080096819A1 (en) 2006-05-02 2008-04-24 Allozyne, Inc. Amino acid substituted molecules
JP2010526091A (ja) 2007-04-30 2010-07-29 インテザイン テクノロジーズ, インコーポレイテッド 癌の処置のための生物学的な標的基の改変
WO2009038195A1 (ja) * 2007-09-20 2009-03-26 Riken 変異体ピロリジル-tRNA合成酵素及びこれを用いる非天然アミノ酸組み込みタンパク質の製造方法
GB0721291D0 (en) * 2007-10-30 2007-12-12 Medical Res Council Methods and compositions
JP2012518431A (ja) * 2009-02-25 2012-08-16 ビッグテック プライベート リミテッド チクングニア検出用のプローブおよびプライマー
GB2470770A (en) 2009-06-04 2010-12-08 Medical Res Council Incorporation of unnatural amino acids having an orthogonal functional group into polypeptides using orthogonal tRNA/tRNA synthetase pairs
GB0917242D0 (en) * 2009-10-01 2009-11-18 Medical Res Council Acetyl lysine incorporation with tRNA synthetase
GB0917240D0 (en) * 2009-10-01 2009-11-18 Medical Res Council Incorporation of methyl lysine into poiypeptide
CN102971329B (zh) 2010-04-15 2016-06-29 麦迪穆有限责任公司 用于治疗增殖性疾病的吡咯并苯并二氮杂卓
ES2527536T7 (es) * 2010-04-27 2016-03-08 Synaffix B.V. Compuestos de ciclooctina fusionada y su uso en reacciones clic sin metales
US20120077186A1 (en) 2010-05-07 2012-03-29 Oregon Health & Science University Use of cysteine-derived suppressor trnas for non-native amino acid incorporation
WO2011156686A2 (en) 2010-06-11 2011-12-15 The Regents Of The University Of Colorado, A Body Corporate Method for synthesizing a cyclic multivalent peptide using a thiol-mediated reaction
JP5951644B2 (ja) 2011-02-03 2016-07-13 エー エム ベー エル シクロオクチニル又はトランス−シクロオクテニル類似基を含む非天然型アミノ酸及びその使用
GB201110815D0 (en) * 2011-06-24 2011-08-10 Medical Res Council Incorporation of subtituted lysines into polypeptides
EP2753607B1 (en) * 2011-09-09 2016-04-13 Berry And Associates, Inc. Bicyclo[6.1.0]non-4-yne reagents for chemical modification of oligonucleotides
GB201201100D0 (en) 2012-01-20 2012-03-07 Medical Res Council Polypeptides and methods
EP2852664B1 (en) 2012-05-18 2017-09-06 Medical Research Council Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase.
SI3584255T1 (sl) 2012-08-31 2022-05-31 Sutro Biopharma, Inc Modificirane aminokisline, ki vsebujejo azido skupino
SG10201702387YA (en) 2012-09-24 2017-04-27 Medimmune Ltd Cell lines
GB2528227A (en) 2014-03-14 2016-01-20 Medical Res Council Cyclopropene amino acids and methods
GB201419109D0 (en) 2014-10-27 2014-12-10 Medical Res Council Incorporation of unnatural amino acids into proteins
CN107614689A (zh) * 2015-03-27 2018-01-19 昆士兰大学 用于将非天然氨基酸并入蛋白质中的平台
GB201817444D0 (en) 2018-10-26 2018-12-12 Res & Innovation Uk Methods and compositions
EP3868882A1 (en) * 2020-02-21 2021-08-25 European Molecular Biology Laboratory Archaeal pyrrolysyl trna synthetases for orthogonal use

Also Published As

Publication number Publication date
CN108410827A (zh) 2018-08-17
IN2014DN09922A (enExample) 2015-08-14
HK1208704A1 (en) 2016-03-11
WO2013171485A1 (en) 2013-11-21
JP2015523965A (ja) 2015-08-20
CN104718285A (zh) 2015-06-17
BR112014028588B1 (pt) 2023-03-21
CA2873793A1 (en) 2013-11-21
EP2852664B1 (en) 2017-09-06
EP2852664A1 (en) 2015-04-01
US20230340013A1 (en) 2023-10-26
US11732001B2 (en) 2023-08-22
BR112014028588A2 (pt) 2017-06-27
CN108410827B (zh) 2023-05-09
BR112014028588A8 (pt) 2021-06-29
JP6343604B2 (ja) 2018-06-13
US20150148525A1 (en) 2015-05-28
US20200271658A1 (en) 2020-08-27

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